{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,5,13]],"date-time":"2025-05-13T10:04:05Z","timestamp":1747130645273,"version":"3.33.0"},"reference-count":15,"publisher":"International Union of Crystallography (IUCr)","issue":"5","license":[{"start":{"date-parts":[[2015,4,25]],"date-time":"2015-04-25T00:00:00Z","timestamp":1429920000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2015,4,25]],"date-time":"2015-04-25T00:00:00Z","timestamp":1429920000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr E Cryst Commun","Acta Cryst E","Acta Cryst Sect E","Acta Crystallogr E","Acta Crystallogr Sect E","Acta Cryst E Cryst Commun","Acta Cryst Sect E Cryst Commun"],"published-print":{"date-parts":[[2015,5,1]]},"abstract":"<jats:p>Six<jats:italic>N<\/jats:italic>-substituted-phenyl 4-oxo-4<jats:italic>H<\/jats:italic>-chromene-3-carboxamides, namely<jats:italic>N<\/jats:italic>-(2-nitrophenyl)-4-oxo-4<jats:italic>H<\/jats:italic>-chromene-3-carboxamide, C<jats:sub>16<\/jats:sub>H<jats:sub>10<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>5<\/jats:sub>(2<jats:italic>b<\/jats:italic>),<jats:italic>N<\/jats:italic>-(3-methoxyphenyl)-4-oxo-4<jats:italic>H<\/jats:italic>-chromene-3-carboxamide, C<jats:sub>17<\/jats:sub>H<jats:sub>13<\/jats:sub>NO<jats:sub>4<\/jats:sub>, (3<jats:italic>a<\/jats:italic>),<jats:italic>N<\/jats:italic>-(3-bromophenyl)-4-oxo-4<jats:italic>H<\/jats:italic>-chromene-3-carboxamide, C<jats:sub>16<\/jats:sub>H<jats:sub>10<\/jats:sub>BrNO<jats:sub>3<\/jats:sub>, (3<jats:italic>b<\/jats:italic>),<jats:italic>N<\/jats:italic>-(4-methoxyphenyl)-4-oxo-4<jats:italic>H<\/jats:italic>-chromene-3-carboxamide, C<jats:sub>17<\/jats:sub>H<jats:sub>13<\/jats:sub>NO<jats:sub>4<\/jats:sub>, (4<jats:italic>a<\/jats:italic>),<jats:italic>N<\/jats:italic>-(4-methylphenyl)-4-oxo-4<jats:italic>H<\/jats:italic>-chromene-3-carboxamide, C<jats:sub>17<\/jats:sub>H<jats:sub>13<\/jats:sub>NO<jats:sub>3<\/jats:sub>, (4<jats:italic>d<\/jats:italic>), and<jats:italic>N<\/jats:italic>-(4-hydroxyphenyl)-4-oxo-4<jats:italic>H<\/jats:italic>-chromene-3-carboxamide, C<jats:sub>16<\/jats:sub>H<jats:sub>11<\/jats:sub>NO<jats:sub>4<\/jats:sub>, (4<jats:italic>e<\/jats:italic>), have been structurally characterized. All compounds exhibit an<jats:italic>anti<\/jats:italic>conformation with respect to the C\u2014N rotamer of the amide and a<jats:italic>trans-<\/jats:italic>related conformation with the carbonyl groups of the chromone ring of the amide. These structures present an intramolecular hydrogen-bonded network comprising an N\u2014H...O hydrogen bond between the amide N atom and the O atom of the carbonyl group of the pyrone ring, forming an<jats:italic>S<\/jats:italic>(6) ring, and a weak C<jats:sub>ar<\/jats:sub>\u2014H...O hydrogen bond in which the carbonyl group of the amide acts as acceptor for the H atom of an<jats:italic>ortho<\/jats:italic>-C atom of the exocyclic phenyl ring, which results in another<jats:italic>S<\/jats:italic>(6) ring. The N\u2014H...O intramolecular hydrogen bond constrains the carboxamide moiety such that it is virtually coplanar with the chromone ring.<\/jats:p>","DOI":"10.1107\/s2056989015007859","type":"journal-article","created":{"date-parts":[[2015,4,24]],"date-time":"2015-04-24T08:27:59Z","timestamp":1429864079000},"page":"547-554","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":4,"title":["New insights in the discovery of novel<i>h<\/i>-MAO-B inhibitors: structural characterization of a series of<i>N<\/i>-phenyl-4-oxo-4<i>H<\/i>-chromene-3-carboxamide derivatives"],"prefix":"10.1107","volume":"71","author":[{"given":"Ligia R.","family":"Gomes","sequence":"first","affiliation":[]},{"given":"John Nicolson","family":"Low","sequence":"additional","affiliation":[]},{"given":"Fernando","family":"Cagide","sequence":"additional","affiliation":[]},{"given":"Daniel","family":"Chavarria","sequence":"additional","affiliation":[]},{"given":"Fernanda","family":"Borges","sequence":"additional","affiliation":[]}],"member":"329","published-online":{"date-parts":[[2015,4,25]]},"reference":[{"key":"lh5762_bb1","doi-asserted-by":"crossref","first-page":"S1","DOI":"10.1039\/p298700000s1","volume":"2","author":"Allen","year":"1987","journal-title":"J. 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